can this board handle an iPhone 6 in an OtterBox?

I use this clip for the 9.7 iPad 2017 model. It fits this pretty well as a "kneeboard" clip. I use a RAM claw for my iPhone that mounts on the window. RAM works really good and should fit an iPhone 6 with otter box case just fine.

Will this work with a iPad Pro 10.5?

It fits my iPad 9.5 with case and there is at least one inch to spare on each clip.

Would this work with a Microsoft Surface Pro 2?

It will accommodate a tablet and case up to 0.95" thick. Use that as your guide. The Surface Pro 2 is 0.53" thick so consider whatever case you may be using or plan to buy. Otterbox is most recommended.

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Item Package Dimensions L x W x H	8 x 2.2 x 0.3 inches
Package Weight	0.07 Kilograms
Item Weight	9.07 Grams
Brand Name	MyBigClip
Model Name	FBA_MBK
Part Number	FBA_MBK

Myclip My Big Clip

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